CH304979A - Process for the production of a condensation product. - Google Patents

Process for the production of a condensation product.

Info

Publication number
CH304979A
CH304979A CH304979DA CH304979A CH 304979 A CH304979 A CH 304979A CH 304979D A CH304979D A CH 304979DA CH 304979 A CH304979 A CH 304979A
Authority
CH
Switzerland
Prior art keywords
condensation product
hot water
crystalline powder
product forms
chlorophenyl
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Variapat
Original Assignee
Ag Variapat
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ag Variapat filed Critical Ag Variapat
Publication of CH304979A publication Critical patent/CH304979A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
    • C07C309/42—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings

Description

  

  



  Verfahren zur Herstellung eines Kondensationsproduktes.



   Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Kondensationsproduktes der wahrseheinlichen Formel
EMI1.1     
 dadurch gekennzeichnet, dass man N-2- (p   Chlor-phenoxy)-5-chlorphenyl-N'-4-chlor-3-    (trifluormethyl)-phenyl-harnstoff mit einem Sulfonierungsmittel behandelt und die entstandene Sulfonsäure mit einer Natriumverbindung in das Natriumsalz überführt.



   Als Sulfonierungsmittel kommen zum Beispiel in Frage : Oleum, konz. Schwefelsäure oder Chlorsulfonsäure.



   Beispielsweise lässt man auf den aus 3-Tri  fluormethyl-4-chlor-phenyl-isocyanat    und 2  (p-Chlorphenoxy)-5-chlor-anilin    erhaltenen N-2- (p-Chlor-phenoxy)-5-chlor-phenyl-N'-3trifluormethyl-4-chlor-phenyl-harnstoff Sehwefelsäuremonohydrat zwischen-7 und   +12  einwirken.    Hierbei wird ein   Sulfon-    säurerest eingeführt ; nach Neutralisation mit   konz.    Natronlauge entsteht   wahrscheinlieh    die Verbindung der obigen Formel.



   Statt Sehwefelsäuremonohydrat kann man auch Oleum oder Chlorsulfonsäure verwenden.



  Bei letzterem arbeitet man vorzugsweise in einem Losungsmittel, wie z. B. Nitrobenzol.



  Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar   lösliehes    Kri  stallpulver,    das als   Mottenschutzmittel    verwendet werden kann.



      Beispie. :   
80 g   Schwefelsäuremonohydrat    werden auf   -7     gekühlt und unter Rühren langsam 20 g N-2-   (p-Chlorphenoxy)-5-chlorphenyl-N'-4-    chlor-3- (trifluormethyl)-phenyl-harnstoff eingetragen, so dass die Temperatur nicht über   --E-12     steigt. Nach dem Eintragen wird noch ungefähr eine Stunde bei dieser Temperatur weitergerührt, bis eine Probe des Reaktionsgemisches in warmer   verd.    Lauge klar löslich ist.



   Darauf wird das Reaktionsgemisch auf Eis gegossen und mit   konz.    Natronlauge schwach alkalisch gestellt, wobei die Verbindung als Öl ausfällt. Die überstehende Losung wird vom   61    abdekantiert und der Rückstand, in 3000   cm3    95 igem Wasser gelöst, mit wenig Tierkohle filtriert und mit 200 cm3 gesättigter   Kochsalzlosung      ausgesal-    zen. Ausbeute : 16 g.



   Das neue Kondensationsprodukt bildet nach dem Trocknen und Mahlen ein helles, in heissem Wasser klar lösliches kristallines Pulver.



     PATENTANSPR. LTCH    :
Verfahren zur Herstellung eines Kondensationsproduktes der   wahrscheinlichen    Formel
EMI2.1     
 dadurch gekennzeichnet, dass man N-2- (p   Chlorphenoxy)-5-chlor-phenyl-N'-3-trifluor-      methyl-4-ehlor-phenyl-harnstoff    mit einem Sulfonierungsmittel behandelt und die entstandene Sulfonsäure mit einer Natriumverbindung in das Natriumsalz überführt.  



   Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar   ösliehes    kristallines Pulver, das als Mottenschutzmittel verwendet werden kann. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the production of a condensation product.



   The subject of the present patent is a process for the preparation of a condensation product of the probable formula
EMI1.1
 characterized in that N-2- (p-chloro-phenoxy) -5-chlorophenyl-N'-4-chloro-3- (trifluoromethyl) -phenyl-urea is treated with a sulfonating agent and the sulfonic acid formed is converted into the sodium salt with a sodium compound convicted.



   Suitable sulfonating agents are, for example: oleum, conc. Sulfuric acid or chlorosulfonic acid.



   For example, the N-2- (p-chloro-phenoxy) -5-chloro-phenyl- N'-3trifluoromethyl-4-chlorophenyl urea sulfuric acid monohydrate between -7 and +12 act. A sulfonic acid residue is introduced here; after neutralization with conc. Sodium hydroxide solution is likely to form the compound of the above formula.



   Instead of sulfuric acid monohydrate, oleum or chlorosulfonic acid can also be used.



  In the latter one works preferably in a solvent, such as. B. nitrobenzene.



  The new condensation product forms a light-colored crystalline powder that dissolves clearly in hot water and can be used as a moth repellent.



      Example :
80 g of sulfuric acid monohydrate are cooled to -7 and 20 g of N-2- (p-chlorophenoxy) -5-chlorophenyl-N'-4-chloro-3- (trifluoromethyl) phenyl urea are slowly added with stirring, so that the temperature does not rise above --E-12. After the addition, stirring is continued for about an hour at this temperature until a sample of the reaction mixture is clearly soluble in warm dilute lye.



   The reaction mixture is then poured onto ice and acidified with conc. Sodium hydroxide solution made weakly alkaline, whereby the compound precipitates as an oil. The supernatant solution is decanted from 61 and the residue, dissolved in 3000 cm3 of 95% water, filtered with a little animal charcoal and salted out with 200 cm3 of saturated sodium chloride solution. Yield: 16 g.



   After drying and grinding, the new condensation product forms a pale crystalline powder that is clearly soluble in hot water.



     PATENT CLAIM. LTCH:
Process for the preparation of a condensation product of the probable formula
EMI2.1
 characterized in that N-2- (p-chlorophenoxy) -5-chlorophenyl-N'-3-trifluoromethyl-4-chlorophenylurea is treated with a sulfonating agent and the sulfonic acid formed is converted into the sodium salt with a sodium compound convicted.



   The new condensation product forms a pale crystalline powder which is clear in hot water and which can be used as a moth repellent.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. gelöst, mit wenig Tierkohle filtriert und mit 200 cm3 gesättigter Kochsalzlosung ausgesal- zen. Ausbeute : 16 g. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. dissolved, filtered with a little animal charcoal and salted out with 200 cm3 of saturated sodium chloride solution. Yield: 16 g. Das neue Kondensationsprodukt bildet nach dem Trocknen und Mahlen ein helles, in heissem Wasser klar lösliches kristallines Pulver. After drying and grinding, the new condensation product forms a pale crystalline powder that is clearly soluble in hot water. PATENTANSPR. LTCH : Verfahren zur Herstellung eines Kondensationsproduktes der wahrscheinlichen Formel EMI2.1 dadurch gekennzeichnet, dass man N-2- (p Chlorphenoxy)-5-chlor-phenyl-N'-3-trifluor- methyl-4-ehlor-phenyl-harnstoff mit einem Sulfonierungsmittel behandelt und die entstandene Sulfonsäure mit einer Natriumverbindung in das Natriumsalz überführt. PATENT CLAIM. LTCH: Process for the preparation of a condensation product of the probable formula EMI2.1 characterized in that N-2- (p-chlorophenoxy) -5-chlorophenyl-N'-3-trifluoromethyl-4-chlorophenylurea is treated with a sulfonating agent and the sulfonic acid formed is converted into the sodium salt with a sodium compound convicted. Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar ösliehes kristallines Pulver, das als Mottenschutzmittel verwendet werden kann. The new condensation product forms a light, crystalline powder that is clear in hot water and can be used as a moth repellent.
CH304979D 1950-04-29 1950-04-29 Process for the production of a condensation product. CH304979A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH299707T 1950-04-29
CH304979T 1950-04-29

Publications (1)

Publication Number Publication Date
CH304979A true CH304979A (en) 1955-01-31

Family

ID=25734094

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304979D CH304979A (en) 1950-04-29 1950-04-29 Process for the production of a condensation product.

Country Status (1)

Country Link
CH (1) CH304979A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0765305A1 (en) * 1994-06-02 1997-04-02 Smithkline Beecham Corporation Anti-inflammatory compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0765305A1 (en) * 1994-06-02 1997-04-02 Smithkline Beecham Corporation Anti-inflammatory compounds
EP0765305A4 (en) * 1994-06-02 1997-09-03 Smithkline Beecham Corp Anti-inflammatory compounds

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